I hope to use my VA loan to buy a duplex to live rent free or close to it  while saving to prepare to repeat the process.

the conditions are varied but majority of blds are classified as D bld and "high" crime neighborhoods high for maine not usa but some sporadic improvements are being realized around court house, canal by river, canal by rt 495, kennedy park, and ice arena by high school. outside this area is much safer and better quality overall conditions, neighborhoods esp near bates college, or closer to highway. more sfr and less multis.many use local long term experienced property management teams unless your strong experienced landlord with systems in place. i have rented too and be inside many lewiston buildings. some transplants have cultural programming like keeping or killing or processing livestock in apartments cupboards and trash accumulation is issue. i have dealt with many lewiston applicants and my experience many with high percent of eviction and or conviction history or both. most are limited by section 8 rules. many my tenants were on younger side, and many had mmj cards and smoke indoors. allow friends couch surf, but some are entrepreneurial but have wrong product. deals can be had. but don't scrimp on professional inspections, or onsite interviews. buildings can be fixed much easier than tenants can.be very careful of flipping single family homes in this tree block area. it wont likely be sold to live in homeowner but rented out by displaced local.

@Maxwell MurphyIf you can heavily subsidized or live rent free, it’s a good chance it’s a good deal!

My main goal of purchasing this property is to be able to live rent free while I save up money to start buying more properties.

What are some unique characteristics of the Chicago apartment rental market, that might surprise a transplant?

We are actually AZ natives who transplanted to UT.

Because of my low income on paper, the only loan for which I can qualify now or in the future is an asset-based one, thus, in the future I wouldn't be able to easily access the equity through a HELOC or refi.The only debt I will have is 5 mortgages; I live rent-free in a room in one of the 5 properties; and the section 8 guaranteed rents for 4 of those, plus the reliable short-term rents from the high-end rooming house, cover the debt service and will cash flow $84,000 (or a proportionate value as rents and expenses rise) for the next 10 years, at which time I'll be 61.

Our municipal taxes are paid quarterly, so I don't have a steady monthly cash in and cash out.So, rentals allows us to live rent rent with the extra cash flow as a pension. 

I assisted in the finding and purchasing of the property with the goal of helping our mother live rent free with some cash-flow for living expenses.

So far, my husband and I love the idea of being able to somehow purchase the duplex that we are in, live in the one we are currently in and then live rent free because the one next to us.